메뉴 건너뛰기




Volumn 50, Issue 23, 2007, Pages 5608-5619

Three-dimensional quantitative structure-activity relationships and activity predictions of human TRPV1 channel antagonists: Comparative molecular field analysis and comparative molecular similarity index analysis of cinnamides

Author keywords

[No Author keywords available]

Indexed keywords

CAPSAICIN; CINNAMAMIDE; CINNAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1; VANILLOID RECEPTOR 1 ANTAGONIST;

EID: 36148932970     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070261k     Document Type: Article
Times cited : (21)

References (37)
  • 1
    • 33644639744 scopus 로고    scopus 로고
    • TRP channels in disease
    • re8, 1-9
    • Nilius, B.; Voets, T.; Peters, J. TRP channels in disease. Sci. STKE 2005, 2005, re8, 1-9.
    • (2005) Sci. STKE , vol.2005
    • Nilius, B.1    Voets, T.2    Peters, J.3
  • 2
    • 0036183319 scopus 로고    scopus 로고
    • Molecular basis for species-specific sensitivity to "hot" chili peppers
    • Jordt, S.-E.; Julius, D. Molecular basis for species-specific sensitivity to "hot" chili peppers. Cell 2002, 108, 421-430.
    • (2002) Cell , vol.108 , pp. 421-430
    • Jordt, S.-E.1    Julius, D.2
  • 4
    • 0032101210 scopus 로고    scopus 로고
    • A capsaicin-receptor antagonist, capsazepine, reduces inflammation-induced hyperalgesic responses in the rat: Evidence for an endogenous capsaicin-like substance
    • Kwak, J. Y.; Jung, J. Y.; Hwang, S. W.; Lee, W. T.; Oh, U. A capsaicin-receptor antagonist, capsazepine, reduces inflammation-induced hyperalgesic responses in the rat: Evidence for an endogenous capsaicin-like substance. Neuroscience 1998, 86, 619-626.
    • (1998) Neuroscience , vol.86 , pp. 619-626
    • Kwak, J.Y.1    Jung, J.Y.2    Hwang, S.W.3    Lee, W.T.4    Oh, U.5
  • 5
    • 0030781343 scopus 로고    scopus 로고
    • Ruthenium red and capsazepine antinociceptive effect in formalin and capsaicin models of pain in mice
    • Santos, A. R.; Calixto, J. B. Ruthenium red and capsazepine antinociceptive effect in formalin and capsaicin models of pain in mice. Neurosci. Lett. 1997, 235, 73-76.
    • (1997) Neurosci. Lett , vol.235 , pp. 73-76
    • Santos, A.R.1    Calixto, J.B.2
  • 6
    • 0037215646 scopus 로고    scopus 로고
    • The VR1 antagonist capsazepine reverses mechanical hyperalgesia in models of inflammatory and neuropathic pain
    • Walker, K. M.; Urban, L.; Medhurst, S. J.; Patel, S.; Panesar, M.; Fox, A. J.; McIntyre, P. The VR1 antagonist capsazepine reverses mechanical hyperalgesia in models of inflammatory and neuropathic pain. J. Pharmacol. Exp. Ther. 2003, 304, 56-62.
    • (2003) J. Pharmacol. Exp. Ther , vol.304 , pp. 56-62
    • Walker, K.M.1    Urban, L.2    Medhurst, S.J.3    Patel, S.4    Panesar, M.5    Fox, A.J.6    McIntyre, P.7
  • 7
    • 4644339264 scopus 로고    scopus 로고
    • TRPV1 and the gut: From a tasty receptor for a painful vanilloid to a key player in hyperalgesia
    • Holzer, P. TRPV1 and the gut: From a tasty receptor for a painful vanilloid to a key player in hyperalgesia. Eur. J. Pharmacol. 2004, 500, 231-241.
    • (2004) Eur. J. Pharmacol , vol.500 , pp. 231-241
    • Holzer, P.1
  • 8
    • 0029319957 scopus 로고
    • Quantitative structure-agonist activity relationships of capsaicin analogues
    • Klopman, G.; Li, J. Quantitative structure-agonist activity relationships of capsaicin analogues. J. Comput.-Aided Mol. Des. 1995, 9, 283-294.
    • (1995) J. Comput.-Aided Mol. Des , vol.9 , pp. 283-294
    • Klopman, G.1    Li, J.2
  • 9
    • 0031260659 scopus 로고    scopus 로고
    • Using artificial neural networks to classify the activity of capsaicin and its analogues
    • Hosseini, M.; Maddalena, D. J.; Spence, I. Using artificial neural networks to classify the activity of capsaicin and its analogues. J. Chem. Inf. Comput. Sci. 1997, 37, 1129-1137.
    • (1997) J. Chem. Inf. Comput. Sci , vol.37 , pp. 1129-1137
    • Hosseini, M.1    Maddalena, D.J.2    Spence, I.3
  • 13
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer, R. D., III; Patterson, D. E.; Bunce, J. E. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 5959-5967
    • Cramer III, R.D.1    Patterson, D.E.2    Bunce, J.E.3
  • 14
    • 0027944195 scopus 로고
    • Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity
    • Klebe, G.; Abraham, U.; Mietzner, T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J. Med. Chem. 1994, 37, 4130-4146.
    • (1994) J. Med. Chem , vol.37 , pp. 4130-4146
    • Klebe, G.1    Abraham, U.2    Mietzner, T.3
  • 15
    • 85128245996 scopus 로고    scopus 로고
    • Cho, S.-J.; Sun, Y. FLAME: A program to flexibly align molecules. J. Inf. Model. 2006, 46, 298-306. FLAME is implemented as a C++ program, using OpenEye toolkits, OEChem and CASE, available at http://www.eyesopen.com.
    • Cho, S.-J.; Sun, Y. FLAME: A program to flexibly align molecules. J. Inf. Model. 2006, 46, 298-306. FLAME is implemented as a C++ program, using OpenEye toolkits, OEChem and CASE, available at http://www.eyesopen.com.
  • 17
    • 0344778061 scopus 로고
    • Semianalytic treatment of solvation for molecular mechanics and dynamics
    • Still, W. C.; Tempczyk.; A.; Hawley, R. C.; Hendrickson, T. Semianalytic treatment of solvation for molecular mechanics and dynamics. J. Am. Chem. Soc. 1990, 112, 6127-6129.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.4
  • 18
    • 36148982142 scopus 로고    scopus 로고
    • Tripos Associates, Inc. Sybyl, 7.1 ed.; St. Louis, MO.
    • Tripos Associates, Inc. Sybyl, 7.1 ed.; St. Louis, MO.
  • 19
    • 36148960751 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Jr, Stratmann, R. E, Burant, J. C, Dapprich, S, Millam, J. M, Daniels, A. D, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Johnson, B. G, Chen, W, Wong, M. W, Andres, J. L, Head-Gordon, M, Replogle, E. S, Pople, J. A. Gaussian 98, revision A.11.3; Gaussian, Inc, Pittsburgh, PA, 1998
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11.3; Gaussian, Inc.: Pittsburgh, PA, 1998.
  • 21
    • 0001797110 scopus 로고
    • Rapid generation of high quality approximate 3D molecular structures
    • Pearlman, R. S. Rapid generation of high quality approximate 3D molecular structures. Chem. Des. Aut. News 1987, 1, 5-7.
    • (1987) Chem. Des. Aut. News , vol.1 , pp. 5-7
    • Pearlman, R.S.1
  • 23
    • 49149147973 scopus 로고
    • Iterative partial equalization of orbital electronegativity - A rapid access to atomic charges
    • Gasteiger, J.; Marsili, M. Iterative partial equalization of orbital electronegativity - A rapid access to atomic charges. Tetrahedron 1980, 36, 3219-3228.
    • (1980) Tetrahedron , vol.36 , pp. 3219-3228
    • Gasteiger, J.1    Marsili, M.2
  • 24
    • 0001041959 scopus 로고    scopus 로고
    • Fast, efficient generation of high-quality atomic charges. AM1-BCC model: I. Method
    • Jakalian, A.; Bush, B. L.; Jack, D. B.; Bayly, C. I. Fast, efficient generation of high-quality atomic charges. AM1-BCC model: I. Method. J. Comput. Chem. 2000, 21, 132-146.
    • (2000) J. Comput. Chem , vol.21 , pp. 132-146
    • Jakalian, A.1    Bush, B.L.2    Jack, D.B.3    Bayly, C.I.4
  • 25
    • 0024716284 scopus 로고
    • Atomic physico-chemical properties for three dimensional quantitative structure-activity relationships. IV. Additional parameters for hydrophobic and dispersive interactions and their appplication for the superposition of certain naturally occurring antibiotics
    • Viswanadhan, V. N.; Ghose, A. K.; Revankar, G. R.; Robins, R. K. Atomic physico-chemical properties for three dimensional quantitative structure-activity relationships. IV. Additional parameters for hydrophobic and dispersive interactions and their appplication for the superposition of certain naturally occurring antibiotics. J. Chem. Inf. Comput. Sci. 1989, 29, 163-172.
    • (1989) J. Chem. Inf. Comput. Sci , vol.29 , pp. 163-172
    • Viswanadhan, V.N.1    Ghose, A.K.2    Revankar, G.R.3    Robins, R.K.4
  • 26
    • 0027672324 scopus 로고
    • Sample-distance partial least squares: PLS optimized for many variables
    • Bush, B. L.; Nachbar, J., R. B. Sample-distance partial least squares: PLS optimized for many variables. J. Comput.-Aided Mol. Des. 1993, 7, 587-619.
    • (1993) J. Comput.-Aided Mol. Des , vol.7 , pp. 587-619
    • Bush, B.L.1    Nachbar, J.R.B.2
  • 27
    • 0029655006 scopus 로고
    • Cross-validated R2-guided region selection for comparative molecular field analysis: A simple method to achieve consistent results
    • Cho, S. J; Tropsha, A. Cross-validated R2-guided region selection for comparative molecular field analysis: A simple method to achieve consistent results. J. Med. Chem. 1995, 38, 1060-1066.
    • (1995) J. Med. Chem , vol.38 , pp. 1060-1066
    • Cho, S.J.1    Tropsha, A.2
  • 28
    • 0034676326 scopus 로고    scopus 로고
    • HIV-1 protease inhibitors: Influence of calculated inhibitor-enzyme binding affinities on the statistical quality of 3D-QSAR CoMFA models
    • Jayatilleka, P. R. N.; Nair, A. C.; Zauhar, R.; Welsh, W. J. HIV-1 protease inhibitors: Influence of calculated inhibitor-enzyme binding affinities on the statistical quality of 3D-QSAR CoMFA models. J. Med. Chem. 2000, 43, 4446-2251.
    • (2000) J. Med. Chem , vol.43 , pp. 4446-2251
    • Jayatilleka, P.R.N.1    Nair, A.C.2    Zauhar, R.3    Welsh, W.J.4
  • 29
    • 3042524904 scopus 로고    scopus 로고
    • Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model. J. Phys. Chem. 1993, 97, 10269-10280.
    • Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model. J. Phys. Chem. 1993, 97, 10269-10280.
  • 30
    • 1542267774 scopus 로고    scopus 로고
    • Resiniferatoxin binds to the capsaicin receptor (TRPV1) near extracellular side of the S4 transmembrane domain
    • Chou, M. Z.; Mtui, T.; Gao, Y.-D.; Kohler, M.; Middleton, R. E. Resiniferatoxin binds to the capsaicin receptor (TRPV1) near extracellular side of the S4 transmembrane domain. Biochemistry 2004, 43, 2501-2511.
    • (2004) Biochemistry , vol.43 , pp. 2501-2511
    • Chou, M.Z.1    Mtui, T.2    Gao, Y.-D.3    Kohler, M.4    Middleton, R.E.5
  • 31
    • 0027291395 scopus 로고    scopus 로고
    • Walpole, C. S.; Wrigglesworth, R.; Bevan, S.; Campbell, E. A.; Dray, A.; James, I. F.; Perkins, M. N.; Reid, D. J.; Winter, J. Analogues of capsaicin with agonist activity as novel analgesic agents: Structure-activity studies. 1. The aromatic A-region. J. Med. Chem. 1993, 36, 2362-2372.
    • Walpole, C. S.; Wrigglesworth, R.; Bevan, S.; Campbell, E. A.; Dray, A.; James, I. F.; Perkins, M. N.; Reid, D. J.; Winter, J. Analogues of capsaicin with agonist activity as novel analgesic agents: Structure-activity studies. 1. The aromatic "A-region". J. Med. Chem. 1993, 36, 2362-2372.
  • 32
    • 27844465429 scopus 로고    scopus 로고
    • Proton activation does not alter antagonist interaction with the capsaicin-binding pocket of TRPV1
    • Gavva, N. R.; Tamir, R.; Klinosky, L.; Norman, M. H.; Louis, J.-C.; Wild, K.; Treanor, J. J. S. Proton activation does not alter antagonist interaction with the capsaicin-binding pocket of TRPV1. J. Med. Chem. 2005, 68, 1524-1533.
    • (2005) J. Med. Chem , vol.68 , pp. 1524-1533
    • Gavva, N.R.1    Tamir, R.2    Klinosky, L.3    Norman, M.H.4    Louis, J.-C.5    Wild, K.6    Treanor, J.J.S.7
  • 33
    • 23644447370 scopus 로고    scopus 로고
    • Lee, J.; Jin, M.-K.; Kang, S.-U.; Kim, S. Y.; Lee, J.; Shin, M.; Hwang, J.; Cho, S.; Choi, Y.-S.; Choi, H.-K.; Kim, S.-E.; Suh, Y.-G.; Lee, Y.-S.; Kim, Y.-H.; Ha, H.-J.; Toth, A.; Pearce, L. V.; Tran, R.; Szabo, T.; Welter, J. D.; Lundberg, D. J.; Wang, Y.; Lazar, J.; Pavlyukovets, V. A.; Morgan, M. A.; Blumberg, P. M. Analysis of structure-activity relationships for the B-region of N-(4-t-butylbenzyl)-N′-[4- (methylsulfonylamino)benzyl]-thiourea analogues as TRPV1 antagonists. Bioorg. Med. Chem. Lett. 2005, 4143-4150
    • Lee, J.; Jin, M.-K.; Kang, S.-U.; Kim, S. Y.; Lee, J.; Shin, M.; Hwang, J.; Cho, S.; Choi, Y.-S.; Choi, H.-K.; Kim, S.-E.; Suh, Y.-G.; Lee, Y.-S.; Kim, Y.-H.; Ha, H.-J.; Toth, A.; Pearce, L. V.; Tran, R.; Szabo, T.; Welter, J. D.; Lundberg, D. J.; Wang, Y.; Lazar, J.; Pavlyukovets, V. A.; Morgan, M. A.; Blumberg, P. M. Analysis of structure-activity relationships for the "B-region" of N-(4-t-butylbenzyl)-N′-[4- (methylsulfonylamino)benzyl]-thiourea analogues as TRPV1 antagonists. Bioorg. Med. Chem. Lett. 2005, 4143-4150
  • 34
    • 84906381446 scopus 로고    scopus 로고
    • Accelrys, Inc, San Diego, CA
    • Insight II; Accelrys, Inc.: San Diego, CA (www.accelrys.com).
    • Insight II
  • 35
    • 36148998422 scopus 로고    scopus 로고
    • Improving docking accuracy through molecular mechanics generalized Born optimization and scoring
    • Lee, M.; Sun, Y. Improving docking accuracy through molecular mechanics generalized Born optimization and scoring. J. Chem. Theory Comput. 2007, 3, 1106-1119.
    • (2007) J. Chem. Theory Comput , vol.3 , pp. 1106-1119
    • Lee, M.1    Sun, Y.2
  • 36
    • 0021107965 scopus 로고
    • Solvent accessible surfaces of proteins and nucleic acids
    • Connolly, M. L. Solvent accessible surfaces of proteins and nucleic acids. Science 1983, 221, 709-713.
    • (1983) Science , vol.221 , pp. 709-713
    • Connolly, M.L.1
  • 37
    • 0000381930 scopus 로고    scopus 로고
    • Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: An analysis of ALOGP and CLOGP methods
    • Ghose, A. K.; Viswanadhan, V. N.; Wendoloski, J. J. Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: An analysis of ALOGP and CLOGP methods. J. Phys. Chem. A 1998, 102, 3762-3772.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 3762-3772
    • Ghose, A.K.1    Viswanadhan, V.N.2    Wendoloski, J.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.